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B.K. Banik, F.F. Becker / Bioorg. Med. Chem. 9 (2001) 593±605
(t, 2H), 3.62±3.78 (m, 6H), 7.57±7.78 (m, 3H), 7.89±8.02
(m, 2H), 8.11±8.21 (m, 1H), 8.57±8.68 (d, 1H), 8.70±8.88
(m, 2H), 9.10 (s, 1H), 9.39 (s, 1H); 13C NMR (CDCl3) d
29.29, 32.93, 42.27, 45.76, 66.44, 66.77, 114.66, 120.79,
121.47, 123.68, 123.78, 125.95, 126.37, 126.54, 126.65,
128.30, 128.36, 130.36, 131.18, 131.70, 132.29, 170.91,
171.69. MS 413 (M+). UV (CH2Cl2) lmax 272.00 ( 46948).
IR cmÀ1 (neat) 3261, 1647, 1630, 1539, 1512, 1438, 1362,
1300, 1272, 1235. Anal. (C26H24N2O3) C, H, N.
1619, 1540, 1510, 1478, 1439, 1240. Anal. (C28H28N2O2)
C, H, N.
N-(60-chrysenyl)-4-(10-heptamethyleneimine)-butane-1,4-
dicarboxamide (6i). Melting point 120±123 ꢀC. 1H
NMR (CDCl3) d 1.48±1.82 (m, 10H), 2.92±3.0 (t, 2H),
3.0±3.06 (t, 2H), 3.44±3.47 (t, 2H), 3.52±3.59 (t, 2H),
7.59±7.71 (m, 3H), 7.91±7.96 (m, 2H), 8.24±8.25 (d, 1H),
8.63±8.65 (d, 1H), 8.76±8.81 (m, 2H), 9.46 (s, 1H), 9.61
(s, 1H). MS 439 (M+). IR cmÀ1 (neat) 3265, 1725, 1674,
1620, 1539, 1511, 1477, 1441, 1359, 41332, 1286, 1236,
1206. Anal. (C29H30N2O2) C, H, N.
N-(60-chrysenyl)-4-(10-thiomorphonyl)-butane-1,4-dicar-
boxamide (6e). Melting point 200±202 ꢀC. 1H NMR
(CDCl3) d 2.55±2.70 (m, 4H), 2.80±2.93 (t, 2H), 2.93±
3.07 (t, 2H), 3.73±3.88 (t, 2H), 7.55±7.75 (m, 2H), 7.90±
8.00 (m, 2H), 8.10±8.20 (d, 1H), 8.60±8.68 (d, 1H), 8.70±
8.82 (m, 2H), 9.08 (s, 1H), 9.37 (s, 1H); 13C NMR
(CDCl3) d 27.81, 28.16, 30.01, 33.38, 45.15, 48.58,
115.16, 121.20, 121.87, 124.08, 124.20, 126.39, 126.96,
128.71, 130.77, 131.59, 132.09, 132.69, 171.08, 172.13.
MS 429 (M+). UV (CH2Cl2) lmax 271.97 (2 39562). IR
cmÀ1 (neat) 3267, 1628, 1539, 1509, 1464, 1441, 1366,
1288, 1240. Anal. (C26H24N2O2S) C, H, N.
N-(60-chrysenyl)-4-(10-piperidinyl)-but-2-ene-1,4-dicarb-
oxamide (9a). Melting point 162±163 ꢀC. 1H NMR
(CDCl3) d 1.50±1.70 (m, 6H), 3.50±3.60 (t, 2H), 3.65±
3.75 (t, 2H), 6.39±6.49 (d, 1H), 6.58±6.68 (d, 1), 7.55±
7.79 (m, 3H), 7.90±7.99 (m, 2H), 8.35±8.41 (m, 1H),
8.61±8.68 (d, 1H), 8.72±8.85 (m, 2H), 9.60 (s, 1H), 11.05
(s, 1H); 13C NMR (CDCl3) d 24.15, 25.40, 26.25, 30.85,
42.74, 47.72, 114.39, 120.71, 123.53, 123.66, 125.97,
126.23, 126.37, 126.46, 126.52, 126.65, 128.16, 128.25,
129.11, 130.34, 131.03, 131.81, 132.19, 132.97, 162.83,
165.23. MS 409 (M+). UV (CH2Cl2) lmax 271.22
(43499). IR cmÀ1 (neat) 3243, 1683, 1667, 1603, 1543,
1510, 1475, 1442, 1410, 1393, 1366, 1275, 1259, 1241.
Anal. (C27H24N2O2) C, H, N.
N-(60-chrysenyl)-4-(10-piperidinyl)-pentane-1,4-dicarboxa-
mide (6f). Melting point 169±170 ꢀC. H NMR (CDCl3)
1
d 1.62 (s, 6H), 2.17±2.23 (m, 2H), 2.59±2.66 (t, 2H), 3.46
(m, 2H), 3.63 (m, 2H), 7.59±7.73 (m, 4H), 7.92±7.97 (m,
2H), 8.23±8.28 (m, 1H), 8.63±8.68 (d, 1H), 8.75±8.85 (m,
2H), 8.97 (s, 1H), 9.39 (s 1H); 13C NMR (CDCl3) d
21.77, 24.48, 25.63, 26.57, 32.04, 36.88, 42.79, 46.80,
115.03, 120.79, 121.60, 123.69, 123.74, 126.03, 126.45,
126.55, 126.63, 126.70, 128.28, 128.33, 130.36, 131.17,
131.74, 132.16, 170.96, 172.34. MS 425 (M+). UV
(CH2Cl2) lmax 271.4 nm ( 86956). IR cmÀ1 (neat) 3252,
1651, 1635, 1538, 1510, 1479, 1466, 1441, 1417, 1276,
1260, 1226. Anal. (C28H28N2O2) C, H, N.
N-(60-chrysenyl)-4-(40-N-methylpiperazinyl)-but-2-ene-1,
4-dicarboxamide (9b). Melting point 98±99 ꢀC. 1H
NMR d 2.29 (s, 3H), 2.40±2.51 (m, 4H), 3.61±3.66 (t,
2H), 3.76±3.81 (t, 2H), 6.43±6.64 (dd, 2H), 7.59±7.78
(m, 4H), 7.94±7.99 (m, 2H), 8.31±8.35 (m, 1H); 13C
NMR (CDCl3) d 41.69, 45.84, 46.50, 54.34, 54.82,
114.50, 120.77, 121.89, 123.68, 126.11, 126.22, 126.48,
126.58, 126.64, 126.81, 128.22, 128.27, 128.34, 130.44,
131.13, 131.70, 132.27, 133.96, 163.67, 165.38. MS 424
(M+). UV (CH2Cl2) lmax 270.6 nm (2 39500). IR cmÀ1
(neat) 3240, 1667, 1614, 1543, 1510, 1472, 1441, 1290,
1259, 1241. Anal. (C27H25N3O2) C, H, N.
N-(60-chrysenyl)-4-(10-N-methylpiperazinyl)-pentane-1,4-
dicarboxamide (6g). Melting point 176 ꢀC. 1H NMR
(CDCl3) d 2.11±2.18 (m, 2H), 2.27 (s, 3H), 2.36±2.38 (m,
4H), 2.50±2.57 (t, 2H), 2.63±2.69 (t, 2H), 3.49 (m, 2H),
3.67 (m, 2H), 7.62±7.65 (m, 4H), 7.85±7.90 (m, 2H),
8.08±8.10 (m, 1H), 8.52±8.56, 8.64±8.72, and 8.79 (d, t,
and s, 4H), 9.16 (s, 1H); 13C NMR (CDCl3) d 21.54,
31.98, 36.69, 41.52, 45.47, 45.90, 54.64, 55.07, 115.29,
120.76, 121.49, 123.61, 123.77, 126.10, 126.56, 126.67,
126.80, 128.20, 128.36, 130.33, 131.18, 131.56, 132.26,
171.15, 172.18. MS 438 (M+). UV (CH2Cl2) lmax 271.2
nm ( 32570). IR cmÀ1 (neat) 3255, 1651, 1623, 1540,
1440, 1291, 1253, 1237. Anal. (C28H29N3O2) C, H, N.
N-(10-pyrenyl)-4-(10-piperidinyl)-butane-1,4-dicarboxamide
(16a). Melting point 158±160 ꢀC. H NMR (CDCl3) d
1
1.64 (m, 6H), 2.91 (m, 2H), 2.95 (m, 2H), 3.46 (m, 2H),
3.71 (m, 2H), 7.9-8.29 (m, 8H), 8.63 (d, 1H), 9.72 (s,
1H); 13C NMR (CDCl3) d 24.39, 25.60, 26.28, 29.80,
33.15, 43.23, 46.52, 120.83, 121.20, 122.70, 124.69,
124.80, 125.10, 125.14, 125.20, 125.98, 126.37, 127.37,
127.55, 128.43, 130.89, 131.38, 170.48, 171.97. MS 385
(M+). UV (CH2Cl2) lmax 244.2 nm (2 21134). IR cmÀ1
(neat) 3263, 1685, 1620, 1557, 1520, 1488, 1457, 1442,
1416, 1370, 1307, 1275, 1263, 1227. Anal. (C25H24N2O2)
C, H, N.
N-(60 -chrysenyl)-4-(10 -hexamethyleneimine)-butane-1,4-
dicarboxamide (6h). Melting point 140 ꢀC. 1H NMR
(CDCl3) d 1.50±1.70 (m, 4H), 1.70±1.86 (m, 4H), 2.85±
2.98 (t, 2H), 2.98±3.08 (t, 2H), 3.45±3.58 (t, 2H), 3.60±
3.70 (t, 2H), 7.55±7.75 (m, 2H), 7.88±8.00 (m, 2H), 8.20±
8.27 (m, 2H), 8.58±8.68 (d, 1H), 8.72±8.85 (m, 2H), 9.45
(s, 1H), 9.58 (s, 1H); 13C NMR (CDCl3) d 26.70, 27.01,
27.49, 28.68, 29.75, 33.23, 46.36, 47.95, 114.39, 120.75,
121.76, 123.58, 123.69, 125.78, 126.35, 126.40, 126.49,
128.25, 128.30, 130.34, 131.06, 132.01, 132.21, 171.95,
172.18. MS 438 (M+). UV (CH2Cl2) lmax 270.012 nm
(2 83764). MS 425 (M+). IR cmÀ1 (neat) 3265, 1674,
N-(10-pyrenyl)-4-(40-N-methylpiperazinyl)-butane-1,4-di-
carboxamide (16b). Melting point 152±153 ꢀC. 1H
NMR (CDCl3) d 2.30 (s, 3H), 2.40±2.44 (t, 4H), 2.91 (m,
2H), 2.96±2.97 (t, 2H), 3.52±3.57 (t, 2H), 3.75±3.80 (t,
2H), 7.95±8.26 (m, 8H), 8.55±8.59 (d, 1H), 9.41 (s, 1H);
13C NMR (CDCl3) d 29.43, 32.75, 41.87, 45.20, 45.89,
54.51, 54.78, 120.77, 121.53, 122.96, 124.69, 125.05,
125.10, 125.96, 126.43, 127.27, 127.53, 128.53, 130.78,
131.09, 131.28. MS 400 (M+). UV (CH2Cl2) lmax 244.2